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“Don’t want Google snooping on your Valentine?” That’s the question Microsoft is asking today in its latest “Scroogled” video. Last week, Microsoft picked up its anti-Google campaign to put the spotlight on privacy and the fact that Gmail looks at your email’s content to better target its contextual ads. Those ads were, to put it mildly, very aggressive. For Valentine’s day, Microsoft just launched a new ad that shows the evil “Gmail Man” opening and reading love letters as he delivers them to their recipients (though on a positive note, he does throw some random coupons into them to sweeten the deal). The Outlook postman, naturally, just delivers the letters without looking at them.

The message here doesn’t really need any explanation, but I had a chance to talk to Stefan Weitz, Microsoft’s director of Online Services and the lead spokesperson for the Scroogled campaign yesterday to discuss these ads.

Weitz was very open about the fact that this is indeed a very negative campaign. The reason for this, he argues, is that Microsoft is trying to get people to pay attention to its products like Outlook.com and Bing. Google, Weitz said, “is a habit” that even his girlfriend can’t quite break.

The problem for Microsoft, according to him, is that just focusing on features and speed may work when trying to attract early adopters, but for mainstream users, it matters for more how they feel about a product and that it is aligned with their values. With the Scroogled campaign, Microsoft is trying to get people to stop and at least reconsider their options.

Whether these videos really get people to stop and think about whether they want to use Google or not remains to be seen. While it’s hard to like the secret agent-like Gmail Man in today’s video, it’s at least a slightly more lighthearted take on the this message. Overall, I still think Microsoft would be better off if it just highlighted where its products outperform Google, but Weitz is probably also right that Microsoft also needs to have a more visceral message that doesn’t just focus on “features and speed.”

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OverviewMicrosoft is an American multinational corporation that develops, manufactures, licenses, supports and sells computer software, consumer electronics and personal computers and services. Its best known software products are the Microsoft Windows line of operating systems, Microsoft Office office suite, and Internet Explorer web browser. Its flagship hardware products are Xbox game console and the Microsoft …